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Title: Tin-free radical mediated C-C bond formation via the Xanthate transfer
Authors: Goh, Kelvin Kau Kiat
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Issue Date: 2015
Source: Goh, K. K. K. (2015). Tin-free radical mediated C-C bond formation via the Xanthate transfer. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: Formation of carbon-carbon bonds had been by far the most researched and refined objective in organic synthesis. On the contrary, the use of free-radical chemistry in this area had thus been limited to tin-mediated protocols which were gradually losing popularity due to toxicity and purification issues. Xanthates, a class of thiocarbonylthio compounds have found remarkable application in both inter- and intra-molecular tin-free radical additions to simple and un-activated olefins. In this thesis, the use of xanthates is further explored and renewed through combination with other types of radical chemistry previously employed with tin-based initiators. The goal is to develop novel tin-free solutions in the C-C bond formation for the synthesis of highly functionalized molecules which had otherwise been plagued by acid-base problems in ionic chemistry. This concept is briefly demonstrated by a few free-radical alternatives to enolate chemistry involving ketones, lactones and thiolactones.
DOI: 10.32657/10356/62948
Schools: School of Physical and Mathematical Sciences 
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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